N′-(2-Methoxy­benzyl­idene)nicotinohydrazide

Ping Wang; Cong Li; Yong-Qing Su

doi:10.1107/S1600536810003831

. 2010 Feb 6;66(Pt 3):o542. doi: 10.1107/S1600536810003831

N′-(2-Methoxybenzylidene)nicotinohydrazide

Ping Wang ^a, Cong Li ^a, Yong-Qing Su ^a,^*

PMCID: PMC2983706 PMID: 21580313

Abstract

The title compound, C₁₄H₁₃N₃O₂, was prepared by the reaction of 2-methoxybenzyaldehyde with nicotinic acid hydrazide in methanol. The dihedral angle between the benzene and pyridine rings is 5.9 (3)°. In the crystal structure, molecules are linked by intermolecular N—H⋯O hydrogen bonds, leading to the formation of chains along the c axis; adjacent chains are linked via C—H⋯O and C—H⋯N hydrogen bonds.

Related literature

For general background to Schiff base compounds, see: Archibald et al. (1994 ▶); Harada et al. (1999 ▶); Ogawa et al. (1998 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Sun et al. (2009 ▶); Wen et al. (2009 ▶).

Experimental

Crystal data

C₁₄H₁₃N₃O₂
M _r = 255.27
Tetragonal,
a = 9.3264 (13) Å
c = 15.594 (3) Å
V = 1356.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.983, T _max = 0.985
6623 measured reflections
1519 independent reflections
1313 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.084
S = 1.06
1519 reflections
176 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003831/ci5028sup1.cif

e-66-0o542-sup1.cif^{(15.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003831/ci5028Isup2.hkl

e-66-0o542-Isup2.hkl^{(74.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.90 (1)	2.05 (2)	2.897 (2)	157 (3)
C4—H4⋯O1ⁱⁱ	0.93	2.58	3.469 (3)	160
C11—H11⋯N3ⁱⁱⁱ	0.93	2.53	3.429 (4)	164
C13—H13⋯N1ⁱ	0.93	2.56	3.487 (3)	176

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors acknowledge support by the Science and Technology Department of Yunnan Province, the Program of Yunnan Province’s Young-Middle Aged Reserve Scientific and Technological Principal Culture Plan (grant No. 2006PY01–50) and the fund of Yunnan Province’s Applied Research Plan (grant No. 2006E0032M).

supplementary crystallographic information

Comment

Schiff bases have been received much attention in recent years (Ogawa et al., 1998; Archibald et al., 1994; Harada et al., 1999). As a further investigation of the structures of Schiff base compounds, the title new compound is reported here.

In the title compound, the dihedral angle between the benzene ring and the pyridine ring is 5.9 (3)°. All the bond lengths are comparable with the similar Schiff bases reported previously (Wen et al., 2009; Mohd Lair et al., 2009; Sun et al., 2009).

In the crystal structure, molecules form chains running along the c axis through intermolecular N—H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental

2-Methoxybenzaldehyde (1.0 mmol, 136 mg) and nicotinic acid hydrazide (1.0 mmol, 137 mg) were dissolved in methanol (30 ml). The mixture was stirred at room temperature for 1 h to give a colourless solution. After keeping the solution in air for 3 d, colourless block shaped crystals were formed.